3-Bromo-5-(trifluoromethyl)benzoic acid → 3-bromo-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-5-(trifluoromethyl)benzamide

HRID 878249Notes

Reaction equation

HRID 878249 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:5]([N:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[O:22][CH3:23])[CH3:8])=[O:6].[Br:31]C1C=C(C=C(C(F)(F)F)C=1)C(O)=O>>[Br:31][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:5]([N:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[O:22][CH3:23])[CH3:8])=[O:6]

Participants

3

Reactant 2

HCID 110867883-Bromo-5-(trifluoromethyl)benzoic acidHCID 70663278HCID 70663278, compound

Product 1

HCID 706633173-bromo-N-(4-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)-N-methyl-5-(trifluoromethyl)benzamide

Procedure

The title compound was prepared in analogy to example 90, from 4-(4-fluoro-2-methoxyphenyl)-N-methylpyridin-3-amine (example 129, intermediate) and 3-bromo-5-(trifluoromethyl)benzoic acid after a reaction time of 22 hours. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (ISCO) system eluting with a gradient of n-heptane:EtOAc (100:0 to 20:80). Off-white solid (68%). MS (ESI): m/z=483.03 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 20:80)

Sources & evidence

ORD record
ord-cdf2c5479e40419699d13b9b71f635b8
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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